He's been in this over 5 years while you've only been in this a little over 5 months. He's invested his time as well as his money, not to mention his full support (he flew into Seattle last year for the first annual SHM).
Cowboy is one of the longest LONGS reeltime has and he's been one of its greatest supporters. "Confidence" may just be his middle name!
Those of us who have been around here a bit longer than you are just getting a little weary, that's all.
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